Ethanol → 2-(3-Bromo-5-methoxyphenyl)acetic acid

HRID 621451Notes

Reaction equation

HRID 621451 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([O:11][CH3:12])[CH:5]=[C:6](CC#N)[CH:7]=1.[OH-:13].[Na+].[CH2:15]([OH:17])[CH3:16]>>[Br:1][C:2]1[CH:3]=[C:4]([O:11][CH3:12])[CH:5]=[C:6]([CH2:16][C:15]([OH:13])=[O:17])[CH:7]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 212429652-(3-Bromo-5-methoxyphenyl)acetonitrile

Product 1

HCID 212429042-(3-Bromo-5-methoxyphenyl)acetic acid

Procedure

A mixture of 5-bromo-3-methoxyphenylacetonitrile (22.6 g, 0.1 m) and 10% aqueous sodium hydroxide (300 ml) in ethanol (225 ml) is heated to 95° for 18 hours. The mixture is concentrated in vacuo, acidified with 10% hydrochloric acid and extracted with ethyl acetate. The ethyl acetate extract is washed, dried with sodium sulfate and concentrated in vacuo to give 5-bromo-3-methoxyphenylacetic acid.

Workup

  1. temperatureis heated to 95° for 18 hours
  2. concentrationThe mixture is concentrated in vacuo
  3. extractionextracted with ethyl acetate
  4. extractionThe ethyl acetate extract
  5. washis washed
  6. dry with materialdried with sodium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f8d8aac79f9944a39050130b8f950566
Source dataset
uspto-grants-1989_04
Patent number
US04824839

Reaction notes

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